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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:15 UTC
HMDB IDHMDB0014738
Secondary Accession Numbers
  • HMDB14738
Metabolite Identification
Common NameMonobenzone
DescriptionMonobenzone, also known as benoquin or 4-benzyloxyphenol, belongs to the class of organic compounds known as 4-alkoxyphenols. These are phenols that carry an alkoxy group at the 4-position of the benzene ring. Monobenzone is a drug which is used topically to treat the loss of skin color (vitiligo). Monobenzone is the Monobenzone used medically for depigmentation. Following skin depigmentation after topical application of monobenzone, the histological studies indicate similar results as that seen in vitiligo, where the epidermis is intact but with the absence of identifiable melanocytes. Monobenzone is an extremely weak basic (essentially neutral) compound (based on its pKa). Monobenzone occurs as a white, almost tasteless crystalline powder, soluble in alcohol and practically insoluble in water. The same action is thought to be responsible for the depigmenting effect of the drug in humans. Monobenzone, applied topically to the skin, is used as a depigmenting agent inhibitting melanin produced by polymerization of oxidation products of tyrosine and dihydroxyphenyl compounds. Monobenzone works by permanently removing color from normal skin located around skin with vitiligo.
Structure
Data?1582753215
Synonyms
ValueSource
4-(Benzyloxyl)phenolChEBI
4-(Phenylmethoxy)phenolChEBI
4-Benzyloxy-phenolChEBI
4-BenzyloxyphenolChEBI
Benzyl p-hydroxyphenyl etherChEBI
Hydroquinone benzyl etherChEBI
Hydroquinone monobenzyl etherChEBI
MonobenzonaChEBI
MonobenzonumChEBI
MONOBENZYL ether OF hydroquinoneChEBI
Monobenzyl hydroquinoneChEBI
p-(Benzyloxy)phenolChEBI
p-Hydroxyphenyl benzyl etherChEBI
BenoquinKegg
BenzoquinHMDB
Benzyl hydroquinoneHMDB
Monobenzyl ether hydroquinoneHMDB
Novo-depigmanHMDB
ICN brand OF monobenzoneHMDB
Agerite albaHMDB
Chemical FormulaC13H12O2
Average Molecular Weight200.2332
Monoisotopic Molecular Weight200.083729628
IUPAC Name4-(benzyloxy)phenol
Traditional Namesuperlite
CAS Registry Number103-16-2
SMILES
OC1=CC=C(OCC2=CC=CC=C2)C=C1
InChI Identifier
InChI=1S/C13H12O2/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-9,14H,10H2
InChI KeyVYQNWZOUAUKGHI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 4-alkoxyphenols. These are phenols that carry an alkoxy group at the 4-position of the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class4-alkoxyphenols
Direct Parent4-alkoxyphenols
Alternative Parents
Substituents
  • 4-alkoxyphenol
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point110 - 118 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.039 g/LNot Available
LogP3.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
logP3.08ALOGPS
logP3.24ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.91ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.11 m³·mol⁻¹ChemAxon
Polarizability21.91 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9110000000-025722658da7cc1290d6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9330000000-3eaa17644c5b236db8daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1190000000-3595b5030a4ebc2347c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-9380000000-a97bc5e4be8acb8419d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-5b165e47c98443994ad9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e7b44cd98d5e6c8549d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-0900000000-1bff4b9e2c443589d41dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8900000000-278866faee3a03db76a8Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00600 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00600 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00600
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7356
KEGG Compound IDC14244
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMonobenzone
METLIN IDNot Available
PubChem Compound7638
PDB IDNot Available
ChEBI ID34380
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
P14679
Molecular weight:
60392.69
References
  1. Chen YR, Y-Y R, Lin TY, Huang CP, Tang WC, Chen ST, Lin SB: Identification of an Alkylhydroquinone from Rhus succedanea as an Inhibitor of Tyrosinase and Melanogenesis. J Agric Food Chem. 2009 Mar 25;57(6):2200-5. doi: 10.1021/jf802617a. [PubMed:19159217 ]